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<h1><a href="https://archiveofourown.org/works/22638439">wanna see if it's true</a> by <a class='authorlink' href='https://archiveofourown.org/users/jk_rockin/pseuds/jk_rockin'>jk_rockin</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>the skirt game [2]</td></tr>

<tr><td><b>Category:</b></td><td>The Umbrella Academy (TV)</td></tr>

<tr><td><b>Genre:</b></td><td>Anal Fingering, Anal Sex, Barebacking, Crossdressing, Dirty Talk, Implied/Referenced Rape/Non-con, M/M, Sex Games, Sibling Incest</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-02-09</td></tr>

<tr><td><b>Updated:</b></td><td>2020-02-09</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-04-28 11:08:37</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>2,658</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/22638439</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/jk_rockin/pseuds/jk_rockin</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>"I suppose I should be grateful you've learned to at least teleport to <i>outside</i> the bathroom door," said Diego, turning off the tap and drying his hands on a towel.</p><p>"Your infantile obsession with privacy is irrelevant," Five said. "Why won't any of you idiots fuck me?"</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Number Five | The Boy/Diego Hargreeves</td></tr>

<tr><td><b>Series:</b></td><td>the skirt game [2]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/1628518</td></tr>

<tr><td><b>Comments:</b></td><td>7</td></tr>

<tr><td><b>Kudos:</b></td><td>197</td></tr>

</table>

<a name="section0001"><h2>wanna see if it's true</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>Although this story is entirely consensual, it does make extensive reference to the previous story in this series, which is not. If dirty talk referencing rape is not for you, then this story is not for you. If I didn't tag for something and you think I should have, let me know. Title also from "Me &amp; U", by Cassie.</p><p>(yes, this is the artist formerly known as findyourfortunefalling.)</p>
    </blockquote></div><div class="userstuff module">
    
    <p>The pop and the clomp of shoes on floorboards were all the warning Diego got before the bathroom door burst open, revealing Five, glowering, in his Academy uniform. Well, no, not his uniform. His uniform came with shorts, and the one he wore featured an ill-fitting skirt.</p><p>"Has everyone in this family gone blind, or are you all conspiring to mock me?" Five was still pretty small, his post-averted-apocalypse growth spurt still very much in progress, but he filled the doorway like a kitten puffing itself up to look big.</p><p>"I suppose I should be grateful you've learned to at least teleport to <i>outside</i> the bathroom door," said Diego, turning off the tap and drying his hands on a towel.</p><p>"Your infantile obsession with privacy is irrelevant," Five said. "Why won't any of you idiots fuck me?"</p><p>With more time to process, Diego probably wouldn't have laughed, but a man had limits. Five waited him out, scowling, apparently still intent on an answer. "Too intimidated by your sparkling personality, I guess," Diego said, nudging past Five.</p><p>"This method of signalling sexual availability seems intended to bypass <i>personality</i>, as you put it, entirely," said Five, following Diego down the hall. "But when I arrived for breakfast-"</p><p>"Oh, Jesus," said Diego. "You wore that to breakfast?"</p><p>"Your absence was noted," said Five.</p><p>"I had a long night," Diego said. He'd kept walking pretty much at random, hoping Five would get bored and give up, and found himself in the gallery. Mom was nowhere to be seen; her habits had been harder to predict since they'd come back to the house. "Look, did you want something?"</p><p>"I want to know why nobody is responding to my signalling," said Five. "None of you normally have any impulse control to speak of."</p><p>"Oh, yes, how could we possibly resist you," said Diego, rolling his eyes. "A grouchy kid in a school uniform- what's sexier than that?"</p><p>"I'm not a kid," Five snapped. "I'm twice your age. And I'm not <i>grouchy</i>."</p><p>"Of course not. You're a regular ray of sunshine." Behind him, he heard Five's footsteps come to a halt, and he turned around, taking in the sour twist to Five's jaw, and the tense set to his shoulders. He actually did look upset, which took Diego aback; not much really ruffled Five.</p><p>"Klaus laughed at me," Five said, after a long moment of silence. His expression was still thunderous, but there was a plaintive note in his voice that made him sound... young, kinda, and vulnerable, in a way that stopped Diego in his tracks. “I didn’t even say anything, he just- looked at me, and he <i>laughed</i>.”</p><p>“Klaus can be a dick like that,” said Diego. “Since when do you want it with Klaus, anyway?”</p><p>“That’s not the point,” Five muttered. “I just- I didn’t want-”</p><p>“You didn’t want him to not want you,” Diego said, trying not to let his voice go gentle. Five didn’t answer, just let out a huff of breath and looked away. "And I assume Allison and Luther weren't, uh."</p><p>"They're all wrapped up in each other," said Five. He sneered when he said it, but Five had a whole library of sneers, and this one was downright affectionate. Apparently that was enough to kick him out of feeling sorry for himself; he raised his eyes to Diego's, and took a step toward him, then another, until Diego's retreat backed him into one of the couches arranged along the gallery, and he found himself sitting down with Five looming- trying to loom, anyway- over him. "I got all dressed up special, and they hardly noticed."</p><p>Diego wasn't sure that could be true. For all that the skirt was an awkward length on Five, he looked quite a picture in it, with his blazer unbuttoned, tie loose, and his crisp white shirt all neatly tucked in. He swallowed. "I didn't think Mom had any of the old plaid left," he said, struggling to keep his eyes on Five’s face, and off the strips of extremely bare skin visible between the skirt's hem and the tops of his knee socks.</p><p>“Please, like Grace would put me in something this badly fitted," said Five. He turned his hips sideways, showing Diego where the skirt was cinched in at the back with a safety pin. "It's Vanya's."</p><p>Diego coughed into his fist. The Vanya Incident, as he thought of it- the capital letters helped, for some reason- was not exactly his finest hour, and for all that he'd apologised, he still felt guilty about it. Not guilty enough to have stopped jerking off thinking about how Vanya had felt thrashing under him, her cunt quivering around his cock, but pretty guilty. "Oh," he said lamely. "That's… generous of her."</p><p>"Vanya's been more forthcoming than the rest of you," Five said. "She gave me a very... illuminating report of her own initiation into the family pastime."</p><p>Diego flushed. "If I'd known she didn't know-"</p><p>"Then you would have been as tiresome as you're being now, I'm sure," said Five. "I do know. I'm wearing a skirt. Are you going to fuck me, or what?"</p><p>Five wasn't a kid, that was true. He didn't look quite so much like a kid anymore, either. Regular meals and sleep and not running for his life all the time were filling him out, though he'd probably always be a skinny little thing. He was pretty, too, and there was something thrilling in the vulnerability behind his bravado; Five had to want something pretty bad if he was willing to ask for it.</p><p>"The whole idea is the person in the skirt <i>doesn't</i> choose what gets done to them," Diego said.</p><p>"Wouldn't know," said Five flippantly. "I never got to play. There's lube in my pocket."</p><p>Five had inched into the vee of Diego's legs, and was now close enough to touch. Before he'd consciously decided what he was going to do, Diego found his hand moving up to touch the skirt's side zipper, and felt the shape of a small bottle beneath the fabric. He also felt, as his hand curved to fit around Five's hip, a faint tremor, as though Five were shivering. His other hand, clearly also running ahead of his brain, went directly to one of those strips of exposed skin above Five's socks that had occupied so much of his attention; it was just as soft as it looked, and Five shivered again when he touched him there.</p><p>Inspired by having elicited a reaction out of Five- a rare and treasured commodity- Diego slid his hand further up Five's thigh, feeling that smooth skin under his own rough palms. It was easy, so easy, to keep sliding his hand higher, feeling the muscles tense and shift.</p><p>"Underwear too inefficient for you?" he said, as though Five being naked under his little skirt <i>wasn't</i> making him light-headed with sudden lust.</p><p>"In certain circumstances," said Five, breathlessly. "Please stop fucking around."</p><p>The temptation was there to make another joke, to banter some more, but Five's skin was warm under his hands; Diego could be pretty stupid about some things, but he wasn't an idiot. Tugging at Five's hip, he pulled him off-balance and onto his lap, knees either side of Diego's thighs, skirt fanning out, and fiddled with the pocket to get at the bottle of lube.</p><p>Once he got it out and open, he had to let go of Five to drizzle some on his fingers. It took a certain amount of dexterity to get his hand up under the skirt without making a mess everywhere, but it was worth it; that shudder ran through Five again as Diego's fingers dipped between his cheeks, and he tipped forward to bury his face in Diego's neck as the first finger pushed in.</p><p>That Five was tight inside wasn't surprising, but it sent another rush of blood south anyway. He was warm, too, and hadn't really got the hang of bearing down, so he fluttered and clenched arryhthmically around Diego's finger. "Might want to do this yourself, the next time you put a skirt on," Diego said. Ever the multitasker, he'd worked his free hand up under Five's shirt, and had a palm on his back, not quite holding him. "Makes everything go a lot faster if you're ready beforehand."</p><p>"If I'd wanted my own hands, I wouldn't have bothered with this exercise at all," Five said, muffled against Diego's shoulder. "This is rather more courtesy than you showed Vanya, isn't it?"</p><p>Diego faltered a bit, but rallied, sliding a second finger into Five just this side of too fast. "I really didn't know she didn't know," he said, choosing his words with care. "She's been around more, and I thought, I dunno, maybe Allison had told her about what we used to do, and she wanted in."</p><p>"Your decades of weird confused hate-lust over Vanya had nothing to do with it, I'm sure. I'm almost insulted you're being so careful with me," said Five. He arched back into Diego's fingers, burying them in his ass to the knuckle.</p><p>"I think I can be forgiven being a little gunshy after <i>accidentally raping my sister</i>, thanks," said Diego. "She told you about it, right. What I did to her."</p><p>"She says I drink alone too much," said Five. "Not quite sure how drinking in her company is better, but she's- ah, fuck, yes, another one, come on- she's pretty talkative after a few."</p><p>It did no good to ask. Diego would probably be better off not knowing, and it felt gross to want to know, how Vanya might describe what happened between them. He still wanted to know, though. "What'd she say?" he asked.</p><p>"She told me about the skirt," said Five. He was getting a little dry, so Diego slid his fingers out, and got them wet again. Five's cock was tenting his own skirt up in the front, obscene, like a sight gag from a teen movie; it could wait. "You have Klaus to thank for that, by the way."</p><p>"He- what?"</p><p>"Klaus helped her pick it out." Five hissed between his teeth as Diego pressed all three fingers back in at once, and his balls dragged against Diego's palm as he twisted his hips to accommodate the stretch. "Told her to wear it to the house. Didn't tell her what it meant, of course. He's a dick that way."</p><p>"Yeah," said Diego. He'd have to think about that later, but with the additonal lube, his fingers moved easily in that grasping heat, and the zipper of his jeans was starting to feel like a torture device. Focusing on anything else would have to wait. "What else?"</p><p>"And how you- ah, shit- tossed her around like a ragdoll," Five moaned. His wrist was starting to hurt, but that, too, was hard to concentrate on while he was occupied with the way Five’s back undulated as he fucked himself on Diego's hand. “How you sliced off her panties with one of your knives, and, and-”</p><p>“She tell you she came, just from me fucking her?” Diego murmured in Five’s ear. His thumb nudged up along Five’s perineum, rubbing under his balls in slow circles that made him gasp and twitch. "She's tight inside, just like you, but when she came she clamped down so hard I thought my dick was gonna snap off." Five scoffed, or tried to; it came out more like a whimper, though still kind of pissy. Diego twisted his wrist again, curled his fingers forward so he was rubbing Five's prostate both inside and out, and held him close. "Did she tell you how I filled her up with my come? What a <i>mess</i> I made of her?”</p><p>Letting out a ragged, animalistic noise, Five came, cock jerking and spurting all up the inside of his skirt. He did clench tight around Diego's fingers, squeezing fit to push them right out, but Diego kept them in him while Five shook through his orgasm, only withdrawing them once the shivering stopped. As soon as his hand moved up and out of the way, Five's hands came down to scrabble at the opening of his jeans, uncharacteristically clumsy.</p><p>"Whoa, hey," said Diego, shifting to help get his top button open. "Careful with the goods, there."</p><p>"Not my fault you wear stupid inaccessible clothes," said Five. He yanked roughly at the zip, and slipped his hand through the slit of Diego's boxers to palm at his cock.</p><p>"Oh fuck," said Diego, fighting the urge to hump Five's hand. His fingers, cool and smooth against Diego's aching erection, curved around the shaft and gave it a single, loose-gripped pump, more exploratory than anything. "You know, we don't have to-"</p><p>"Put your fucking dick in me," Five snarled, "or I <i>will</i> snap it off, so help me god."</p><p>Five was bigger now than he had been, but he'd never be in Diego's weight class; it was easy to lift him up and tip him over, landing them both on the floor with a crash. Diego took advantage of Five being briefly winded to shove his jeans down his thighs and retrieve the lube from the couch. Moving in between Five's legs, he ran a slick hand over his cock, hiked Five's knees up, and fucked into him without ceremony.</p><p>He felt even hotter inside, and still so tight Diego was grateful for the time he'd taken to open him up on his fingers. This wasn't going to last long regardless, but it was nice to be able to plant his knees and just use Five's wet, open hole, thrusting gracelessly as he chased his own pleasure.</p><p>Having Five on his back was nice, too. The couches along the gallery were too small to have had him on one on his belly, like he'd had Vanya, and the expressions on his face, all sweet and shocked and overwhelmed, those were really good. Would Vanya have looked like that, if he'd fucked her face-up? He could picture it, imagine her in Five's place under him on the floor, and the thought alongside the reality of Five gasping and wriggling on his cock built and built inside him until he came, pitching forward and spurting deep into Five's ass.</p><p>"Oh, gross," Five said, when Diego composed himself enough to pull out. "Remind me to bring condoms next time. Or wet wipes, at least."</p><p>Diego rolled off Five and onto his back, staring up at the ceiling. God, he felt good. Even the cool air on his cock where it lay, sticky, against his thigh, felt great. Beside him, Five had sat up, and was dabbing at the disaster of spunk all over his crotch with the still-dry edge of his skirt; he was kvetching under his breath, like he did, but his forehead was smooth, his shoulders relaxed, like he felt pretty good, too.</p><p>"Come on, I missed breakfast," said Diego. He put his dick away, zipped his jeans, and got to his feet, holding out a hand to Five, who took it without bothering to wipe the come off his own hand first. "Oh, thanks. And a shower. Shower, then breakfast. And clothes that don't smell like a frat house."</p><p>"This is my only skirt," said Five.</p><p>Diego looked him over. His hair was a mess, all rucked up in the back from being rubbed against the floor, and he had managed to get come on literally every garment he had on, including the knee socks. He looked very thoroughly fucked already, and it was still pretty early in the day.</p><p>"Klaus'll have one," he said eventually. "We can work something out."</p><p>"Shower first, though," said Five, and strode away down the gallery, with a little hitch to his step that made Diego's balls tingle, even though he'd only just got off.</p><p>"Sure," said Diego. "Whatever you like."</p>
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